Bad Timing
by Briony8869
Summary: High School AU - Dean Winchester is kind of sucking at this whole high school thing, unlike his little brother who basically just wins at life. He decides to try to make things better for himself by dating the super foxy Anna, but he finds that he's awkwardly entranced by her little brother.
1. Chapter 1

"C'MON SAMMY! Knock that asshole out!" Dean Winchester roared from the stands at his little brother's basketball game. Some dick on the other team had just personal fouled Sam for about the 80th time, and Dean was just about ready to run out there and punch his lights out.

Ever since Sammy had made the varsity basketball team (as a Sophomore! Sometimes freakish height has its advantages) Dean hadn't missed a game. He'd rescheduled his work shift so he could make this one, and he hated to see some prick on the other team shove his kid brother around.

"Son," said a large man sitting in front of Dean. "That 'asshole' happens to be my nephew."

Dean eyed the guy. He was older, mid-forties maybe, roughly 300 pounds, and looked like the sort of person you'd avoid sitting next to at a truck stop McDonald's.

"Well your nephew's a dick." Dean sneered. He had never got the knack of self-preservation. It just wasn't in his genes.

Several minutes later both Dean and about 6 people around him who had also gotten involved in the fight had been removed from the premises. His ears were ringing and his jaw was sore, but his nose didn't feel broken. Not that the blood pouring out of it made that particularly obvious.

When he reached his house Dean saw one yellowish light was on, bleakly illuminating the kitchen window. _Fuck. _He thought, irrationally. _Dad's home. _

Staunching the flow of blood from his nose with one of his over shirts (self preservation was not a Winchester family virtue, but layers were) Dean shakily opened their kitchen door. He found the room just as empty and messy as he'd left it. No Dad. Of course not.

The only person he had to explain himself to was his stupid kid brother.

"Dean, they had to stop the game because of you! That guy said he was going to sue the school!" Sam yelled, almost as soon as he had stepped into the house. Dean couldn't really maneuver himself to respond very easily, seated on the couch with a self-administered bag of frozen french fries on his face.

"He had it fucking coming!" Dean shouted. "You were the one getting pushed around out there like a little bitch!"

"Dean," Sam ran his hands through his stupid hair that was always in his stupid face. He gave Dean that long suffering expression he'd had down since he was twelve. "That's how you play basketball! It's the ref's job to call this stuff! You can't just assault former Marines!"

"Dude was a Marine?" Dean raised an eyebrow, then laughed. "Shit. Now I feel kind of bad."

"Don't worry, it's not like you landed any punches." Sam sighed. He sat next to Dean on the couch, and Dean settled back into his seat. They sat in awkward silence for a few minutes.

"So, am I suspended?" Dean asked.

"I don't think so. No teachers saw what happened. A bunch of guys on the team did though…" Sam groaned and held his face in his hands, "God, Dean, could just, stop? Please?"

"Stop what?"

"Stop stalking my life! I don't need you at every basketball game. Don't you have like, any of your own friends you could hang out with!"

Dean tensed. What had previously been an awkward silence thickened and became excruciating.

"Go to bed, Sam." He said, coldly, avoiding his brother's gaze and replacing the frozen french fries on his face.

Sam silently did as he was told, and Dean turned on the TV. Dr. Sexy MD was on, but he found that even that dreamy man couldn't hold his attention. _I have friends. _He fumed. _Fuck you I have friends. _

Dean made a point NOT to hang out with Sam and his friends the next several days, and he was forced to accept some harsh truths. First and foremost, he didn't have any friends.

_How did this happen? _Dean thought as he carried his chicken patty lunch tray around the cafeteria, scanning the occupants of the lunch room. _I'm a senior! Where is my group? _But most of the faces happily talking and eating around him were unfamiliar. Here and there he would see someone he recognized. Lisa, for instance, with whom he had had a fling a while back. But from the hideously dark glare she gave him when they made eye contact he figured he'd done something to screw that up.

There was Crowley, that weird kinda goth kid who'd sold him some weed his freshman year. But that was more a business negotiation than a friendship. Even though Crowley raised an inquisitive eyebrow when he saw Dean looking for a place to sit, Dean quickly looked down at his feet. There was somebody else he could find, surely.

But everyone had friends. All of the tables in the cafeteria were filled with happy groups of laughing, socially accepted teenagers who were cheerfully reveling in their own company and completely unaware of Dean Winchester's existence. Almost imperceptibly Dean's jaw clenched, and his swagger increased somewhat. He looked for a table, any table, that wasn't filled with functioning human beings.

Of the whole cafeteria, there was only one table that had a lone occupant.

The dude sitting by himself was pale, with dark, disheveled hair, and some seriously lovely blue eyes. He was weirdly intent with downing his hamburger. He was wearing, wait, was he wearing a tie? Before he could figure out what the hell was going on with that kid though he felt a tap on his shoulder.

"Hey, you looking for a place to sit?" He turned around and looked into the lovely, pale face of a redhead he recognized from math class.

"Oh, uh, yeah. Anna, right?" He said.

"That's me." She smiled, and her whole face lit up. "You've been wandering around for like ten minutes. Jo and I thought you looked lost." She gestured over to where she was sitting with a very cute blonde girl who was looking him over with extreme skepticism.

"I'm not lost, I'm just looking for someplace to sit that isn't full of jerks."

"Well, you were making us sad." Jo said matter of factly. "Sit down, weirdo."

_Yup. _Dean thought. _Still got it._

"Mr. Winchester. What a privilege to see you in class." Mr. Rollins said when Dean took his seat next to Anna in math class. It had been so long since he attended he hadn't even been able to find his notebook. Maybe he'd never even bought one for the class. Some nerds snickered at their teacher's joke and Dean felt kind of uncomfortable.

Anna just smiled at him though, and he remembered who he was.

"Less of a privilege to be here sir." Dean smirked.

His teacher just rolled his eyes and began the lesson. It might as well have been in Latin for all he could understand it. But hey, that was just more of an excuse to ask Anna for tutoring help later. Sammy thought he didn't have any friends huh? He'd make friends. He'd make FRICKIN' HOT lady friends.

Anna had that sort of pale, ethereal look about her that subliminally reminded Dean of something somebody would paint in a Rennaissance portrait. Dean's left over fast food lunches contrasted sharply with her whole wheat pitas filled with arugula and goat cheese, bento boxes, and frickin' sesame salads. He used to watch her eating them in sort of confused admiration, as she'd somehow manage to gracefully eat whatever weird, healthy, Whole Foods looking thing she had packed in her reusable lunchbox that day.

Jo's lunches were usually made up of things Dean could identify as food (zebra cakes, turkey sandwiches, Cheetos) and her conversation was of the salacious variety. If Dean misspoke, Jo would pounce, teasing him mercilessly about anything from his flannel shirts to his pouty model face, which he had honestly never even realized was a thing. Jo would frequently go off on tangents about people that Dean didn't know with Anna, who would laugh and go along with it, but somehow manage to bring the conversation back around to something Dean could participate in.

Anna would smile at Dean sometimes, like she didn't realize she was doing it.

Dean wanted to get all up on that.

As it turned out, Anna beat him to it. They'd been sitting together at lunch for about three weeks, Dean's math attendance had suddenly skyrocketed, and finally one day when he was walking with her after school she turned to face him.

"Dean. We should have dinner."

"What, now? It's three thirty!" Dean responded, brilliantly.

"Um, no Dean. Like a date dinner. Like, see a movie or something. I'm asking you on a date."

"Oh! Um, hell yeah!" Dean responded somewhat sheepishly. Dean's sexual adventures had generally been of the "make-out under the bleachers" or "sneak out the chick's bedroom window in the middle of the night variety". He'd never been asked on a date before. Anna smiled her beautiful smile at him, then kissed his cheek, totally taking him off guard.

"Good. Now I have to go drive my little brother home, but call me later ok?"

Anna waved at Dean and turned to leave. Standing awkwardly in front of her locker, staring at the floor intently and with surprising stillness, was the dark haired kid that Dean had noticed sitting by himself in the cafeteria.

"You ready to go Castiel?" Anna addressed the guy. Her tone was just a little bit too cheerful for a sibling to address another sibling. It was more like the cautious way he spoke to Sammy when he was sure something was wrong.

Castiel nodded silently and with a clean, quick movement picked his backpack up off of the floor and glanced back over his shoulder at Dean.

His eyes were blue and cold and beautiful and Dean felt sort of uncomfortable after meeting them directly.

So that was Anna's brother. Weird family.

Dean went home by himself that night, Sammy was hanging out with his basketball friends. He'd at least called to let Dean know that he'd be out though. Ever since their fight Sammy had been pretty courteous to his older brother, making sure he got up on time, greeting him in the hallways. Dean would sort of give him a douchey upwards nod when they passed, particularly if he was with Anna or Jo. He loved that he could change his brother's expression from apologetic optimism to bitchface in about .3 seconds.

They hadn't been spending so much time together.

His father was out, as usual. John Winchester had sent his oldest son an email two weeks ago that said he would be gone for three days. There had been some breakthrough with the case, he'd written, maybe the doctors would finally pay for whatever it is they had done that had killed their mom. Dean had responded with cheerful positivity, and then tried not to think about it. It wasn't going to come to anything of course, it never did, but there was no point dwelling about it. He made dinner so Sammy would have it ready when he came home, (just in case he didn't eat out with his friends) and once he was done Mr. Mom-ing and cleaning up a bit he left for work. Late shift paid better, and who the fuck needed sleep anyway?

Days passed. Dean's grades bobbed just above passing, Sam won basketball games and drank protein shakes, and Anna told her parents she was spending the night at Jo's house when she and Dean would hook up at his place.

Looking at Anna's pale, naked flesh for the first time Dean felt like he had hit the motherfucking jackpot. Hours ago he'd been standing in front of her father, wearing a suit, and basically doing the good old "lying to adults" dance he'd mastered since he was 6 years old. Anna had slowly descended the grand staircase of her cookie-cutter house wearing a sundress that looked as though it called for knee-socks as an accessory. The whole scene could have been out of a 1950s PSA about keeping your virginity. And yet, he'd hardly had time to shut the Impala's door before Anna's hand was on his crotch, her breath was on his neck, and she whispered in his year that she was horny as fuck.

The Anna who lay in Dean's bed next to him was pale, gorgeous, and wholly unexpected. Underneath her nude toned bra and (Jesus Christ) boy short panties she was all pale skin and delicate curves. He could make out the bones in her ribcage when he ran his hands up her side to feel her sweet, smallish breasts. She still looked like something out of a painting, but having a girl like that go down on you really makes one reassess the virgin/whore dichotomy. Having graceful hands was one thing, having those graceful hands gracefully manage one's dick? Um. Yeah.

Usually when Dean drove up to the house to pick Anna up she came right on out, but for some reason tonight when Dean parked his car there was no slender redhead bounding out the door to greet him. He even texted but Anna didn't appear. He put his best "nice guy" face on in case Anna's dad answered the door and went up to ring the doorbell.

The little guy answered the door.

"Hello Dean." Castiel said. "Please come in." Dean stepped into Anna's golden tinted foyer. Her family had a fucking chandelier dangling in front of their massive aforementioned staircase. It would have been impressive if you didn't know that right next door the neighbors had exactly the same set-up only in a mirror image. Once Dean was fully indoors Castiel continued his greeting. "Anna's upstairs, she's on the phone with Michael." Met with a blank stare from Dean Castiel decided to elucidate. "Our brother. In college. She told me to tell you she would be down momentarily." He spoke with a surprisingly deep voice for such a short little dude, and with an earnestness that begged for mockery.

"Do they pay you for butler duty?" Dean joked.

"No they don't." Castiel responded with the utmost seriousness. His expression was blank, which made it hard to tell if he was joking.

"Oh." Dean replied. Instead of leaving, like a normal person would, Castiel simply stood there, staring at him. The intensity of Cas's whole demeanor made it almost impossible not to meet his eyes. Dean noticed details about Cas, the way his hair was always slightly disheveled and even though he dressed like a square with jackets and ties he never really seemed to be very put together. The silence was thick and uncomfortable, for Dean anyway, and he hastened to fill it with some nonsensical small talk.

"So, you're a sophomore huh? You know my brother?"

"I've seen him." Castiel said. "He's very tall."

"Too fucking true man." Dean replied. Sammy had shot up like a bean sprout the summer between his freshman and sophomore year, far surpassing Dean's height. He hated having to look up to see his little brother's face, but it didn't change anything essential. He was still the one who took care of him.

"He seems to be a very good student." Castiel said.

"Heck yeah he is, he's going to Harvard if I have anything to say about it." Dean boasted. He would have been embarrassed if he knew how much of a mother hen he looked right about then.

"He's very handsome as well. And athletic." Castiel continued in his strange deadpan fashion. It sounded like he was describing a racehorse or something.

"Um, ok." Dean sort of smirked. "If you're so in love with him you should ask him out, bro."

Dean only had a second to watch Castiel's face flush before he heard an admonishing "DEAN!" come from the top of the stairs. Anna was standing there, hand still holding one of her flip flops as though she had been rushing to put it on a second before. Now she looked as though Dean had just told her six-year-old nephew that Santa wasn't real.

Castiel simply blushed furiously and made a quick exit, muttering something about studying.

"What the hell Dean?" Anna growled, purposefully descending the stairs towards her target, who honestly didn't know the hell what.

"I, is he mad? It was a joke!" Dean quickly explained.

Anna didn't elucidate then and there. She didn't speak the entire time Dean drove her to Steak 'n' Shake, choosing instead to stiffly stare out the window. Dean knew what it was like to get the cold shoulder, heck, he'd given it to Sammy enough times. Usually though, he had some idea what the fuck had gone wrong.

Anna remained cold and thoughtful as they were seated, only speaking to order her food. Dean sat in growing discomfort for another ten minutes before she addressed him.

"Dean, Castiel just came out to the family three days ago." Anna said flatly, over a banana milkshake.

"What?" Dean almost choked on his burger. "He's, Cas's gay?"

"Apparently. And he made us promise not to tell anyone." Her brow darkened and she squirted some ketchup on her plate with unnecessary violence. "Damn it Dean, it's been hard enough on him already."

"I didn't know!" Dean responded. "I had no idea!"

"But you made a dumbass gay joke in front of him Dean! What were you thinking?"

"That he would laugh at it and move on with his life!" Dean felt he was getting some unjust blame here. "Dude, if you'd just been cool about it it wouldn't even have been a big deal!"

All that Dean saw when he looked at his girlfriend's face at that moment was impending doom. She was shaking with anger, and didn't seem to be able to speak. Dean imagined if somebody had said something like that to Sammy. He backed off.

A thought occurred to him,

"Hold on, does he really have a crush on Sam?"

"I don't know Dean! He doesn't feel comfortable talking about it. But don't you get it?" There was a tremble in Anna's voice now, "Now he thinks that I told you he was gay and that you think that its something embarrassing."

"Fuck." Dean muttered.

"Do you?" Anna asked, and her voice was dead and cold enough to give Dean goosebumps.

"What?"

"Think that it's bad to be gay?"

"What? Anna! No! Of course not!" He glanced at his girlfriend with some desperation. Anna continued to sip on her shake without looking at him. "I'm not a homophobe! Cas can run after chicks or dudes or whatever he wants. I don't care."

For the first time since Dean had made the joke (It was a JOKE for the love of God!) Anna's expression softened slightly. Dean took his chance.

"If he's going after Sammy though, you'd better warn him, I found some porn on the kid's computer a while back and Casa Erotica 4 is about as hetero as you can get."

Anna's expression shifted from cold anger to vague annoyance and disgust.

"Just saying." Dean continued, popping a fry in his mouth. "He might be barking up the wrong tree there."


	2. Chapter 2

Dean figured he owed Cas an apology for what had happened, but damned if he knew how to go about it.

People, dude. Dean could charm the pants off his girlfriend's parents and convince the school nurse that he had chronic migraines and just couldn't go to English, but he had no gift for sincere human interaction. That was Sam. One time Sam had talked a cop out giving Dean a speeding ticket before the cop had figured out Dean was only 14 years old. Sam was the one who most of Dean's former flings talked about their feelings with. He had the gentle, thoughtful thing going on. Whenever Dean tried to replicate it people backed away like he was some kind of psychopath who was planning on disemboweling them.

"Hey Sammy?" Dean asked, turning down the volume on the tv commercials so he could address Sam in the kitchen. He tried to sound casual.

"Dean, would you mind buying greens the next time you go shopping and not this bagged iceberg lettuce? It's got like the same nutritional content as a glass of water." Sam asked, peeking his head out of the kitchen. There was only the tiniest hint of a whine in his voice.

"I bought lettuce?" Dean responded with an incredulous look.

Sam sighed.

Dean continued.

"So Sam. Can I ask you a question?"

"Sure." Sam continued assembling a somewhat depressing iceberg salad.

"Imagine, hypothetically, that some guy made a really insensitive joke and now wants to apologize without sounding like a jerk."

Once again Sam leaned through the doorframe so that Dean could see his face. His head nearly bumped the top. "Wait, is this about the Jolly Green Giant thing?"

"What?" Dean asked.

"When I was up for that free throw at practice and you went 'HO HO HO GREEN GIANT' like the commercial." Sam explained, sitting on the couch next to his brother and jabbing his fork into his salad. This was the Winchester version of family dinner.

"Oh man I forgot about that!" Dean couldn't contain a snort of laughter at the memory. Sam hadn't worn that green t-shirt to practice since. "No dude, geez, not everything is about you Sam!"

"Did you piss of Anna?" Sam's tanned face crinkled into a smirk.

Dean could either tell Sam that he had made a spectacularly ill timed gay joke to a boy that he didn't really know all that well or he could make something up that sounded like something that he would totally do.

"I called Jo fat." Dean lied.

"Jesus, Dean!" Sam looked positively offended for her. "Are you crazy? And she isn't…"

"That was the joke Sam. It's like when a big fat guy's nickname is Tiny. I thought it would be funny."

Sam looked at his older brother as though he were a bottom dwelling creature deserving of nothing but pity and disdain.

"Look, Dean, you've gotta go big on this one. Buy her flowers, do the whole shtick." He raised a hand as Dean started to protest, "I know you hate that chick-flick stuff but girls like it. It's flattering."

"I don't think Anna would be into me buying another chick flowers dude." Dean pointed out, and he was pretty damn sure Cas wouldn't like that particular gift either. _Here, gay dude, have some fucking flowers. I've also made you a tutu and a rainbow scarf so that I can be as utterly offensive as possible. _

Sam resumed his thoughtful expression. The last time Dean had asked Sam's advice about anything had been approximately never, so it was scarcely surprising that he was savoring his position of authority. Dean, on the other hand, was practically fidgeting in his seat as his baby brother made a point of collecting his thoughts.

"You're right. No flowers. Just, take her aside at school, explain why exactly you're an idiot, and tell her you're sorry. Let Anna know that you're doing it too. Maybe buy her a cookie or something."

Dean sighed. "Do I have to say I'm an idiot?"

"YES." Sam said, staunchly. "That's like, the whole point of the thing dude."

Iron Chef America had come back on so Dean turned the volume back up on the tv. Softly, under his breath, Dean said,

"Sorry I started a fight at your basketball game."

"It's no big deal man." Sam replied using his super little brother hearing or something. "Are you gonna buy me a cookie?" He asked hopefully.

"Don't push your luck." Dean muttered. "I'll buy you lettuce."

The next day at school came and Dean approached it hesitantly. He took his supplies from his locker without the company and conversation of Anna, which was abnormal. At this stage in their relationship she had made herself a fixture of his morning routine, meeting him pretty much as he walked in the door of the school and hovering pleasantly while he got he stuff together. This morning he was discouragingly alone. He scribbled in the margins of his notebook instead of listening to his teachers and he eyed the clock as lunch hour approached.

Finally, it was lunchtime. Dean walked through the lunchroom with determination, not swagger, actual determination. Sam said "hey" as he walked past and Dean responded with a smile. Jo and Anna made space for him to sit in his now usual spot but he strode directly past them, to the table where Castiel sat alone.

"Hey Cas." Dean said.

"Um, hello Dean." Castiel replied. He looked as weird as he usually looked, dressed like he wished this was one of those schools that had uniforms, but even then he'd probably be breaking the code somehow.

"Can I sit with you today?" Dean asked.

"I…" Cas's eyes narrowed, his forehead furrowed, and his head tilted ever so slightly to one side. At that moment he was a puppy, trying to figure out an unfamiliar command given by his master. "No." he responded.

Dean, already halfway descended into a seated position across from the kid, paused awkwardly, almost falling. He decided to just go for it anyway. He sat.

"Are you really mad at me?" Dean asked.

"No." Cas responded, but he turned his blue eyes down to stare at his lunch and wouldn't raise them to meet Dean's.

Dean sighed in resignation and reached into his brown bag lunch. Carefully, deliberately, he removed a wrapped Tollhouse cookie and slid it to the center of the table, like a gambler going all in. Cas looked at the cookie with some confusion, then finally up at his sister's boyfriend.

"Cas. I'm an idiot." Dean began, feeling like one.

"Is that for me?" Cas asked, indicating the cookie.

"Yeah." Dean responded. Cas reached to the center of the table and took it, unwrapping it cautiously as he listened to Dean continue.

"I just wanted to say sorry for being a dick the other day. If you want to ask Sam out go ahead, you can do whatever you want. I really don't care."

"I'm not romantically interested in your brother." Castiel responded, mouth full of cookie.

"Well, all I'm saying is if you were it wouldn't be a big deal. It's all good man. It's none of my business anyway." Dean's little apology speech had sounded a lot better when he practiced it last night. But he noticed that the edges of Castiel's lips turned up almost imperceptibly into something that looked like a smile.

"I never thought you were a homophobe. It was just a joke." Castiel said. He looked down at the table and his fingers nervously played with the edges of the cookie wrapper. "Like when the gym teacher calls the guys 'ladies'."

"And what a great joke that is." Dean acknowledged bitterly.

"You didn't mean what you said to be offensive." Castiel finally looked up and met Dean's eyes, and spoke as though this were a private proclamation made between Dean and himself. "Anna told me that you said it before you knew about me. I'm not angry at you Dean."

What a weird fucking kid. Dean couldn't help but smile at him.

"Well thank goodness for that." Dean laughed.

"I do appreciate your kindness however. And the cookie." Castiel sighed as though pleased that that had gone so well.

"The cookie was Sam's idea actually. I'm no good at this stuff. Hey," Dean leaned over conspiratorially. "Why aren't you interested in Sam? Romantically? You not into tall, good looking, bookish, nice guys?"

Castiel looked at Dean like he was being vaguely silly.

"Dean, Sam's straight." Cas said, with the same certitude he had proclaimed that he was not paid for butler duties.

"Oh yeah." Dean responded, as though this was a fact he had once known but had forgotten. "Ok. Do you mind if I eat with you, or do you still want me to leave?" He asked.

Castiel gave Dean an appraising look. "Wouldn't you rather sit with my sister?"

Dean glanced back over his shoulder at Jo and his girlfriend. The two lovely young women were speaking comfortably and rapidly to one another about something Dean probably didn't know anything about. Anna glanced over to her little brother's table, and Dean turned around before he could make out the concern in her eyes. Castiel continued to stare back at him in that way that he had, looking bizarre and alien and yet wholly well meaning. "Well, she's still pissed at me." Dean said, fiddling again with his lunch bag. This time he was the one avoiding eye contact. "You're not. Do you mind?"

"I have no problem with that." Castiel announced, and continued to eat his lunch.

After his grand apology, Dean kept an eye out for Cas around school. He wasn't that hard to pick out, weird little guy with pretty eyes and disheveled hair, usually walking all by himself. Dean would smile and wave at Cas as they passed, and Cas would look sort of confused and give a little nod in return. One time it happened while he was walking down the hallway with Anna. Dean waved and Cas nearly ran into somebody when he smiled in response. Anna grinned and gave her boyfriend's arm a little squeeze.

"It's so nice of you to do that." She smiled at him.

"What, say 'hi'?" Dean shifted uncomfortably, it was odd walking with a girl holding your hand. Sometimes he felt like he needed it back, for like, holding his stuff. Doing its job as a hand.

"Castiel doesn't make friends very easily. I think he's bullied here more than he likes to talk about."

"Bullied!" Dean looked back over his shoulder at Cas, still walking on his own towards his locker. "I thought he was just, kind of…" _Odd? Ethereal? Beautiful? _"Awkward."

"Yeah, people are assholes." Anna sighed. "Anyway, it's nice of you to say hi to him. I'm sure it makes him feel more welcome."

That night at the Winchester household, over a leafy green salad and macaroni and cheese (good fake orange mac-n-cheese from a box, none of that recipe stuff) Dean asked Sam if he had ever heard of Castiel.

"Oh yeah, I've heard of him. He's Anna's brother right? They moved here last year?" Sam responded.

"What's he like? Cas? Anna thinks he's bullied."

Sam looked kind of sad. "Yeah, that's probably true. There's some dumb rumors about him going around."

Dean tensed. "What kind of rumor?"

"You know, the same stuff. People are saying that he's a virgin and he's gay."

"What the hell Sam?" Dean's eyes narrowed into a glare towards his brother. "What kind of gossipy ass friends do you hang out with!"

"Dude, come on. It's just goofing around."

"It's fucking rude." Dean growled. He pointed his fork at Sam, as though to drive home his point. "You're going to befriend the hell out of that kid and you're going to tell your friends to stop being dicks."

"what?" Sam sputtered, "I've never even spoken to him before!"

"Sam. You are in his grade. Everybody likes you, you're like the big tall nice guy everybody likes. If you're nice to him people will start being nice to him. End of story." Dean took another huge bite of Mac 'n' Cheese, and then sat back in his chair smugly.

"You can't just tell me who I have to be friends with…" Sam looked really confused.

"I think I just did. And whatever dude, you're nice, go be nice at him or something. Stop being a bitch."

"…"

"What?"

"jerk."

"attaboy Sammy."

Dean, being a senior, didn't see much of Cas or his brother around school during the course of the day. He maybe passed Cas in the hallway twice a day, and once again after school when he walked Anna to her locker and tried to get a kiss goodbye in before he headed home. Cas would always politely look at the floor for the extent of time Dean had his tongue in Anna's mouth. Lately though Dean had been using this time after school to see how Cas was doing.

"Hey Cas!" He said, mussing up Castiel's hair the way he used to do to Sam's when he could still reach it. "How's it going?"

Castiel had been leaning up against the lockers near Anna's as he always seemed to be at the end of the day. He wiggled away from Dean but made no movement to sort out his hair. It stuck out at odd angles as he gave Dean one of his unreadable looks.

"Why do you call me Cas?" He asked.

Anna, whose arm was still wrapped round Dean's waist, gave him a little attention-demanding squeeze. A week ago that would have been answered by a quick little kiss on the cheek or some other endearing form of PDA. Dean didn't break eye contact with her little brother, so she sighed and went to get her stuff out of her locker.

"I give everybody nicknames." Dean responded.

"Not Anna. Or Jo." Castiel pointed out.

"Those are really short names bro. Jo's got like two letters in it."

"Annie's an acceptable nickname for Anna." Castiel posited.

"THE HELL IT IS." Anna forcefully responded from behind her locker door. Before she could elaborate on exactly how unacceptable the nickname "Annie" is for a girl with red hair her phone buzzed in her pocket. It never ceased to surprise Dean's girlfriend when she got a call, and she always unintentionally made sure everyone around her was aware that it had happened by squeaking like a chipmunk that had just been stepped on. She pulled her purple phone out of her inadequate pocket and flipped it open. Dean was still caught up in his conversation.

"You heard the lady, I don't think she'd be into it." Dean puzzled for a moment. "Maybe Easy A?"

"I'm fairly certain she wouldn't like that one either." Castiel's eyes crinkled in a way that might be interpreted as mischievous, but it wasn't obvious enough to be clear. "Dad used to call her Anna-banana."

"Oh crap, Dean." Anna said, slamming her locker door and making her companions jump.

"Geez, I won't call you that!" Dean promised, but Anna hadn't lifted her eyes from her phone yet.

"Dean, I totally forgot that I volunteered Jo and I to help set up for the debate team competition tonight." Anna was a member of about 12 student organizations, and while she was usually exceptionally good at time management, every once in a while she would overbook. Jo, who was the friend who got dragged along to all the bake sales and fund drives and pep rallies, was less enthusiastically helpful. Anna held up her phone and Dean read the text, "Anna, I will rip your throat out if you are not setting up chairs in the gym right now –Jo"

"Shoot!" Dean said, "you need to get there now?"

"Yeah oh crap I'm so sorry would you mind driving Cas home? I know he has his piano lesson tonight… damn it!" Anna jumped again when her phone vibrated a second time. "Jo's gonna kill me." She muttered.

"Dude, no problem" Dean smiled at his girlfriend, who he was referring to as dude more than anything else these days. "I can drive Cas, it's not like I don't know where you live!"

"Thanks so much Dean." Anna smiled gratefully at him, then turned to throw all her stuff in her bag as fast as she could. "I'll see you later ok?" She yelled as she began to scurry down the hallway towards the gym. "BYE!"

And Dean and Cas were alone together.

"Soooo… do you really want to go to that piano lesson, or do you want to ditch it and get ice cream?" Dean asked, with one of his winning Winchester smirks.

About 20 minutes later Dean sat sucking a straw full of butterscotch milkshake while Cas stared intensely at the sprinkles decorating his cup of soft serve. They were seated on a gray stone bench in front of a little run down soft serve place just a few blocks from Dean's house. The humid air was muggy and miserable. Perfect conditions for fake ice cream.

"I've been meaning to take Anna here for ages." Dean said, sighing in contentment and looking over at Cas. "It's nothing special, just a knock-off Dairy Queen, but Sam and I really like it." Cas was still staring at his sprinkled ice cream cone as though it had just asked him a very difficult math problem and he was trying to work it out in his head.

Dean had his arm stretched out over the back of the bench the way he always did, and his hand was just inches away from the back of Castiel's neck. He could, if he wanted, reach out across the tiny distance separating them and touch Cas's dark, unruly hair. His fingers twitched at the thought, and his eyes locked onto friend's profile. Dean had been told his whole life how handsome he was. He hadn't even had to pay to get his senior pictures done because the photographer guy was so desperate to use the shots in his advertisements. Cas, however, possessed a different kind of attractiveness. It was an asymmetrical handsomeness, not immediately noticeable, but entrancing once you figured out it was there. He was so enthralled that he almost didn't notice that the two of them were being watched. An older couple with that slightly overweight, affordably clothed, white conservative look that populates the Midwest like a disease gave the two of them a dark look. Dean raised his eyebrows at them and scooted a little bit closer to his friend.

"You never mention your father." Castiel said, and BOOM shit got heavy right there.

"Uh, sure I do." Dean responded, "Don't I? I totally do." Dean removed his arm from the back of the bench and took back some of his personal space. The older couple stopped their staring and went back to their sundaes. Dean's leg tapped a nervous rhythm.

"I didn't mean to make you uncomfortable." Castiel said, eyes apprehensive, "I just noticed that Anna spends a lot of time with you and I don't think she's met your parents yet."

"Mom died when I was 6." Dean said. "Bone Cancer." He ungracefully took another swig of butterscotch milk shake.

"I'm sorry." Cas said nervously. Compared to the other 8 billion times Dean had heard that sentiment, he sounded fairly sincere.

"It was a long time ago, I'm fine." Dean's voice was low, grumbly. It had been a while since he'd talked about his family with anybody, and that included Sam.

"And your dad?" Castiel asked.

Dean tensed up. "What the hell Cas? Of COURSE dad's fine, it was like, 10 years ago. Why do you freaking care?"

"Where does he work?" Cas asked, with no reflection in his voice that Dean had just kind of yelled at him.

"He works…" The truth was John Winchester switched jobs so much Dean honestly wasn't sure what he was doing right at that moment. The bills always ended up getting paid, there just wasn't a hell of a lot left over. Dean worked for things like new clothes and Sam's class trips. "He spends a lot of time on the lawsuit." Dean admitted. He'd actively avoided telling Anna about the lawsuit that took up so much of his father's time and money. "The hospital… um, the hospital where mom died really screwed some stuff up. And dad's trying to make sure that they get some freaking retribution for that. Once that's figured out, then things will probably settle down I guess. I mean, I dunno."

"So he isn't around very much?" Cas asked.

"He's busy. It's fine. I can take care of things."

"I don't doubt that, Dean Winchester."

Dean exhaled as he heard Castiel say his full name, in that weird, otherworldly way of his. What was it about that family? His sister could trip and fall down in the middle of the hallway and somehow still look like a ballet dancer or something, and Castiel spoke like something out of a JRR Tolkein novel and yet his deep voice gave Dean all sorts of unforeseen feelings.

"You're a nosy little punk aren't you?" Dean sighed.

"I'm simply curious." Cas said, looking slightly taken aback. "And I don't think I fit any definition of a punk."

After dropping Cas back off at his house, Dean returned to his noticeably empty home. His phone buzzed in his pocket while he was heating up a can of Ravioli (he put a package of Instant Rice out for Sam for whenever he got home. He was probably gonna be hungry, and growing Moose need to eat.) It was Anna, "Dean, can I come over tonight?"

Dean stared at the phone for a second, then flipped it shut, not typing a response. His face was somewhat grim as he ate his meal and flipped on the television. Dr. Sexy was on, fuck yeah. Apparently the good doctor was delivering the baby of a woman with Down Syndrome, but he was having a hard time because the whole hospital was under a bomb threat and the ghost of his dead wife was shrieking at him since it was their anniversary or something. Dean took in Dr. Sexy's broad shoulders, his dark swept hair, and his enticing dark eyes. "Nurse." The doctor said, eyes flashing sexily. "Leave me alone. I've got this."

Dean was suddenly overwhelmed with a feeling of discomfort and he shut the TV off. He flipped his phone back open.

"Anna." He typed. "I need space while I decide if I like dick or pussy." He groaned in frustration as he continued to type. "Cuz yr fucking adorable little bro makes me want to do all kinds of nasty shit."

He stared at the text message for a few seconds, reading and re-reading the statement. He shook his head in irritation and fumbled to erase it as quickly as possible. He threw his phone down onto the coffee table, hard.

"Fuck." He whispered, running his hand through his hair and squeezing his eyes shut. "_Fuck." _


	3. Chapter 3

"So I'm pretty sure my little brother has a crush on you." Anna told Dean, as the two of them sat on the hood of the Impala eating tacos.

Dean coughed, almost cutting the roof of his mouth with the damned shell.

"What?" He asked, no pretense of coolness. Anna had a way of taking him off guard like that.

She grinned at him, teasingly, twisting her legs underneath her in a motion that was way cuter than it had any right to be. Not quite as cute as Cas was when he made his confused face, but that was a whole different issue that Dean was certainly not thinking about.

"Haven't you noticed how he like, always runs downstairs whenever you come to pick me up? He doesn't get the door for anybody else. And if it's not you then he just stands there like a deer in headlights and awkwardly shouts for dad."

Dean shifted uncomfortably on the Impala. He'd been showing up early to pick up Anna because he knew then he could get a few minutes talking to Cas in. That Cas might have been looking forward to their interactions to was a strangely exciting revelation.

"He doesn't have a crush on me, he's just being nice. He's a good kid."

"I don't know Dean, he looks at you more than you realize."

"He looks at everybody! He's like a staring machine!"

"Dude, Dean, I know Castiel pretty well. I know the difference between his usual social awkwardness and his lovestruck stare. He's kind of into you, I think." She grinned at Dean, and why shouldn't she? It was such a silly little thing, Castiel getting crushes. When she'd first noticed Castiel unwittingly staring holes through the back of her boyfriend's head during lunches she had thought he was just measuring up their relationship. But whenever she mentioned Dean's name at home Castiel would do this weird little flush thing and ask for more information. She had even teased him about it slightly once, and his expression afterwards reminded her of how he looked back when he was five and she told him not to tell mom that she'd broken the Tiffany lamp. Cas's face was too darn honest.

It was so nonsensical, Castiel, only recently out of the closet, getting a harmless little crush on her Daytime Television Handsome boyfriend. At least he wasn't thinking about his bullying problems so much anymore. Heck, it was almost a compliment, she was pleased that Castiel had approved so much of her taste in men.

Telling Dean had been a mistake, she could see that from the way he had folded away from her. He was a good guy, and definitely not a homophobe, but it was probably off putting to find out that a dude had a crush on him. He'd better get used to it though, with a face like his.

"He's not gonna do anything about it Dean, don't worry, I'm sure he'll get over it really quick." She touched his shoulder gently and smiled at him.

"Yeah." Dean said quickly, stuffing more of his food in his face. "Totally. It's just a phase. Crushes, you know, you can't do anything about them."

Sam Winchester walked down the hallways of Jefferson high school with none of the forced swagger that bounced his brother aggressively and uncomfortably through the school. If asked he could tell you the names of all the people who surrounded him in the hallway, and probably a little bit extra about who was good at what subject, whose family was going through a hard time, and who was really somebody you needed to stay away from. His fellow students smiled at him, not just his friends, but people he had sat next to in math class a few years ago. Nobody felt uncomfortable approaching Sam Winchester.

"Hey, Castiel? How are you doing?" Sam asked, stepping up to the weird dark haired boy who was switching books into his locker between classes.

Castiel looked up at Sam with a blank expression, only slightly suggesting a level of curiosity.

"You've never asked me that before." He stated.

"Um… no I guess I haven't. Are you doing ok?" Sam tried again.

Castiel shut his locker and craned up to look Sam in the eyes.

"I'm doing perfectly well. I don't understand why you're speaking to me."

His matter of fact demeanor was not exactly what Sam had been expecting from this encounter, and he found he had a hard time sorting out his thoughts to figure out what to say next. It was rare for Sam to be taken off guard like this.

"Just trying to be nice." Sam shrugged, and he began to walk away. After only a few paces though, he heard some rapid footsteps behind him and he found that Castiel had managed to walk up to his side.

"You're Dean Winchester's brother aren't you?" Castiel asked.

"Yup." Sam admitted. "Don't hold it against me."

"You don't look very similar." Cas pointed out.

Sam shrugged with a silly little smile, "I'm much better looking."

"I disagree." Cas responded simply.

"Um." Sam looked at Cas to try to register whether that was meant to be an insult. The guy's face was absolutely unreadable. In good Winchester fashion he decided to smush down any hurt feelings he might have and soldier forward. "He's dating your sister right?" Sam pointed out.

"Yes." Castiel said, softly. His tone sounded somewhat rueful.

"So we're pretty much in-laws at this point. Only not legally." Sam pointed out.

"That doesn't make any sense."

Sam sighed, his expression flickering into bitchface, "I was just thinking, you want to come over for dinner sometime? I feel like our school hasn't been very welcoming to you and your family and maybe you'd like to come eat pizza or something." Sam sighed.

"I'd like that very much." Castiel said, with no hesitation at all.

Dean clenched the steering wheel of his beloved Impala as though that would help him weather the stony glare beating down on him from the passenger's seat. It was about 8:30pm, and he was already driving his girlfriend home from the mall where they had intended to just hang out until whenever. But he had made a dumbass comment about Jo that had leaned too far towards mean rather than funny and Anna had been staring at him in utter silence for the past half hour, responding with one-word answers when Dean tried to extend any olive branches. It wasn't a fight exactly, yet, but it was approaching boiling point. Earlier that week they had gotten into a brief tiff over which side of a banana one should peel, and just that morning the two of them had snapped at each other over what song they should listen to when they shared Anna's iPod.

Anna, who had taken the initiative in just about every other aspect of their relationship, was clearly refusing to start a conversation about what was going wrong between them. And of course, if she was waiting for Dean to take a step in talking about his feelings, well, she was going to be there a while. He stopped at her house, and didn't even have a chance to say, "See ya" before she was out of the car and the door slammed with inconsiderate force.

Dean groaned and turned his music up for the drive back home. Sam would probably be there, maybe the two of them could play some video games or something since so far his Friday night had been such a fucking bust.

He stepped into the house casually checking his phone to see if there was a passive aggressive text. So far nothing.

"Hey Sammy Sam Sam want to… oh."

Dean saw that Sam was sitting on the couch with some dude watching a movie. Dean could recognize after two notes of the score that it was Star Wars.

"Oh, hey bro, didn't mean to interrupt." Dean said backing out of the living room so his brother could chill with his friend in privacy. He turned to get a soda from the kitchen before he planned to retreat into his bedroom, where, defeated, he figured he'd just go to sleep. At nine. Like a four year old.

"Hello Dean."

Dean froze, fridge half open, recognizing the deep voice immediately.

"Cas?" He said, turning around to take a closer look at the boy sitting next to his brother on the couch. He was met by a pair of stunning blue eyes that he recognized immediately. Sam made a scoffing noise.

"Cas?" Sam repeated, "What kind of a nickname is that?"

"Hello Dean." Cas repeated, looking at Dean with his usual blank but vaguely kind expression. "Your brother invited me over for dinner. He ordered pizza, would you like some?"

"What…" Dean stared at Cas, who was still disconcertingly sitting on his couch in his home and being beautiful at an uncomfortably close proximity. Dean took in Cas's fitted black t-shirt and denim jeans, his hair had its usual mussed look. Like every time he looked at Cas, Dean was struck by an urge to just run his fingers through that mussy hair to make it worse. He resisted. "Dude Sam, why didn't you tell me you invited Cas over?"

Sam looked legitimately confused.

"I didn't think about it. I thought you'd be happy, I mean, you know him better than I do." His eyes said, _YOU TOLD ME I HAD TO MAKE FRIENDS WITH HIM, DICKFACE. _

Castiel looked from one brother to the other, talking to Dean again in an attempt to explain the situation further.

"Your brother was upset that I'd never seen Star Wars. He told me you'd be upset as well."

"I'm not ups… wait, you've never seen friggin' Star Wars? Who raised you?" Dean addressed the most pressing point, obviously.

"My parents." Castiel responded honestly.

Dean sighed, as though disgusted that he lived in a world where a weird kid could somehow make it to high school without ever having seen Star Wars. Shrugging his shoulders, he took a piece of pizza from the box and squeezed in on the couch in between his gargantuan baby brother and Castiel.

"Well, prepare to have your mind blown with pure awesome." Dean said, his night suddenly looking like not a complete waste after all. "Unpause that bitch, Sam."

Sam sighed and did as he was told, and Star Wars: A New Hope, resumed motion.

Dean could feel the warmth of Cas's thigh on his, pressed against each other from their close proximity on the couch. There were several possible reasons that the two of them had to be cuddled up so close. It was feasible that Sam just took up too much room for both he and Cas to maintain their personal space. It would also be reasonable to assume that Dean was one of those irritating dudes that you find on public transportation that simply refuse to take up less space than usual, even when cuddling against strangers. It was also feasible (and perhaps likely) that Dean just really liked the feeling of having Cas up so close to him. But this was not the only explanation. Armed with plausible deniability, Dean happily kept his leg where it was.

Cas stared at Star Wars as though this was a cinematic masterpiece that required absolute and rapt attention. Dean enjoyed watching his face taking in every little detail of the film, sometimes tilting slightly in confusion, sometimes smiling at a joke or comment made on screen or by Dean. Every once in a while he caught Cas tearing his eyes away from the TV and peaking a glance at him. If they made eye contact though Cas would flush and hurriedly look straight ahead. After this happened for the third time, Dean moved his leg just a little bit closer to Cas, whom he could feel take a shaky intake of breath at the contact. He was on thin ice here, but Dean had a way of smashing right through thin ice, particularly when his own well-being was at stake.

They watched as Obi Wan taught Luke about the Force. Dean punched the air when Luke met Han Solo for the first time, and paused the film for about a half hour so both he and Sam could trip over themselves explaining why exactly Han shot first. Cas audibly gasped when Princess Leia's home planet was destroyed. Dean patted Cas's shoulder tenderly, er jokingly, assuring him that justice would be served. Right before the rebels were about to take out the Death Star Sam stood up.

"Hey guys, I'm kind of tired, I think I'm going to go to bed."

"Are you kidding? it's the best part!" Dean protested.

"I've seen it at least 60 times Dean." Sam said, yawning. "You two have fun ok?" He stumbled off in the direction of his room, completely blind to the look of panic in both his brother and his guest's face.

Plausible deniability lost, Dean miserably eyed the sudden expanse of freed space on the couch, asking to be filled. The Rebel fighters were on their way. Dean scooted away a bit, leaving some space between himself and Castiel, and finding his right side disappointingly cold without Cas's body heat. Fighter pilots that were indecipherable from one another until about the 8th time you watched the film jabbered on about plot points. Castiel, quietly, almost imperceptibly, reclosed the distance between the two of them. Apart from the sound of laser guns and one of the fighters shouting, "I can't shake him! I can't shake him!" Dean noticed that Cas seemed to be holding his breath.

He turned his head, and Cas met his gaze with his usual intensity. There was a questioning anxiety in his expression that Dean had never seen before. The normally unflappable Castiel seemed, well, flapped? He didn't turn his eyes back to the screen after being caught staring.

Dean reached out and pulled Cas's face towards his, pressing his lips against his friend's with an unanticipated roughness. Cas stiffened and attempted to pull away, and Dean jumped back immediately.

"Fuck Cas, I'm sorry, I didn't... fuck!" Dean's whole body was on fire with nervous energy and he stared down at the ground, weighing and rejecting every possible lie he could say that would explain away his behavior. But there was nothing he could say, you can't just kiss people and then like, say you had a seizure or something. Crushed by embarrassment he continued to stare at the carpet between his shoes as though that could distract him from his humiliation.

"Dean." Cas said, and, his voice seemed more raspy than usual, there was a waver in it. Time slowed down as he reached out a hand and delicately touched the side of Dean's face. He looked at Dean with frightened earnestness, like a kitten examining a new and unfamiliar toy. Maybe it was Dean's nerves, or the nature of their situation, but Cas's touch sent shivers down his spine and he couldn't help but sigh and look directly into his friend's blue gaze.

Cas and Dean stared at one another for approximately one half of a second before Cas grabbed the front of Dean's t-shirt and pulled him in for a second kiss.

The Death Star exploded but at this point nobody noticed. Dean kissed back, cupping the sides of Cas's face and kissing hungrily. The roughness of stubble on Cas's face came as something of a shock after a lifetime of kissing ladies, but Cas's lips were soft and strong and perfect. Cas, inexperienced, was a quick study. He opened his mouth just a little bit and Dean matched his intensity, pressing Cas back into the cushions of the couch. A groan came from the back of Cas's throat, at which point Dean lost all restraint and just had at it like he was under the bleachers.

Cas made out like somebody who'd been desperate for this for years. He pulled himself on to Dean's lap, straddling him and grinding his hips right into Dean's crotch. His hands were everywhere, running through the hair at Dean's neck, stroking his waist, cupping his face. It was Dean's turn to groan as he finally took the opportunity to run his hands through Cas's hair. Cas was starting to figure out what exactly you were supposed to do with your tongue in a situation such as this, and Dean was going nuts. Castiel had no right to be this fucking sexy right at the first shot.

"Dean." Cas whispered into his ear, so close that Dean could feel hot breath on his neck. Cas pressed his lips into Dean's jawline, and Dean wondered why nobody had ever done that to him before. It felt friggin' awesome. His hands ran across Cas's lower back, one hand feeling up Cas's ass and the other starting to go up his shirt, touching his soft skin.

And then Dean's pocket started vibrating, and not because he was happy to see someone.

"Your phone's ringing." Cas said, pulling back a little, the broadest smile on his face Dean had ever seen.

"Screw it." Dean mumbled, pulling the phone out of his pocket to silence it. But as soon as the phone was in his hand he saw Cas's expression shift from lustful happiness to extreme worry and anxiety. He looked at the ID as the phone buzzed again

"Anna." Dean whispered. "Shit."

Cas untangled himself from Dean and stood up, fully and thoroughly removing himself from the moment. He still looked delicious though, his hair was mussed up adorably and his lips were still shiny and pink.

"You should answer," Cas said, "She gets really cranky when you don't."

"Seriously?" Dean asked, stunned, "Now?"

"I don't..." Cas turned his gaze down to the floor. "I should go."

"No Cas, stay…" Dean said,

"Thanks for the pizza and… yeah. Goodbye." Castiel turned awkwardly and pretty much fled for the door, leaving Dean to an angry girlfriend, an awkward boner, and a miserable evening.

Anna and Jo were sitting next to one another on the bed, snuggling fairly close so they could share headphones and watch youtube videos. Intermittently both of them would shriek with laughter, a fact that made their thoughtful use of headphones utterly useless if their intention was not to disturb the other residents of the house. But there is a scientific connection between proximity of teenage girls with their close friends and the general volume of their conversations.

A loud knock on the door made both of them jump, then giggle more as their connected headphones got tangled.

"Darling sister." Anna's older brother Gabe sneered from the door. "Will you please, for the love of all that is holy, SHUT THE HELL UP!"

Anna's entire stance shifted to one of unyielding sassiness. She eyed her blonde elder brother with annoyance.

"Dearest brother." She said, "Go fuck yourself."

But Gabriel did respond to his flesh and blood, having noticed that there was an attractive blonde woman sitting on Anna's bed. All pretense of irritation lost, he leaned against the doorframe with a cocky little head tilt and started speaking to his sister's friend.

"JoAnne! Joey Jo! Josephina! I didn't know you were here!" Gabriel's eyes flicked down to Jo's tank top and he gave her a smirk. "It's been too long!"

Jo gave Gabriel the face that she always gave him during their brief interactions, a brutal glare that combined confusion and irritation and sent less dogged men running home to their computers to blog about how bitchy women are. Gabriel was not such a man though, he was a 20 year old college drop out living at home, with no shame in flirting with his sister's friends. Fortunately, Jo's mother owned a bar, and had trained Jo well in the ways of dealing with creeps.

"Um, yeah." She said, in a tone that suggested she had forgotten exactly who Gabriel was and didn't care to refresh her memory. Then she pressed play on the youtube video and continued watching Toby Turner narrate a video game in an amusing fashion.

Anna would normally have chastised Gabriel in some way for being such a creepy loser, but she had been distracted by Castiel. She had caught a glimpse of her little brother flitting behind Gabriel in the hallway and disappearing into his room like a mouse scrambling back into its den after someone flicks a kitchen light on.

"Castiel!" Anna said, trying to get his attention, but his door had shut already and she couldn't tell if he'd heard.

"What, you'd rather talk to him than me? I'm hurt!" Gabriel said.

"Shut up Gabe." Anna snapped, but she stepped into the hallway to try to follow her little brother. It was too late though, his music had already started playing and he wasn't going to answer the door unless she got her battering ram.

"Has he been acting weird around you?" Anna asked Gabe.

"Hold on, you're asking if CASTIEL is acting weird? Our gay little brother who talks like a robot and dresses like a tax accountant?"

Like about 80% of everything Gabriel said, Anna paid no attention to his response.

"He hasn't said a word to me in three days." Anna said. "I'm worried something happened to him. Like at school."

Anna looked concerned enough that Jo paused the youtube video and took the headphone out of her ear.

"You think he's getting bullied?" Jo asked.

"I KNOW he's getting bullied, I just don't know if it's gotten worse or what. He won't talk to me." Her brow furrowed, switching from anger to frustration. "That little twerp, I could help him out if he'd just tell me what's wrong."

"My strategy to big-siblingdom is to give everybody space." Gabriel said, shoving his way into Anna's room and plopping down next to Jo on the bed. "Cas will come to you when he needs you." He smiled at Jo, like this was a meaningful moment at the end of a 90s sitcom. Jo raised an eyebrow that managed to be both skeptical and judgmental.

Anna rolled her eyes at her older brother and she and Jo managed, through teamwork, to shove him back out to the hallway from whence he came. But even though she and Jo went back to hanging out and avoiding doing homework, she checked the hallway every once in a while to see if there had been any change. Castiel's door stubbornly remained shut.

Castiel lay on his bed in his room, listening to radiohead and trying not to think about how terrible a person he was. Anna absolutely could not be permitted to see him, that went without saying. She would take one look at his face and be able to tell literally everything that had happened. Then, in his imagination, Anna's hair would catch on fire and she would run shrieking at him like a banshee and claw his eyes out with her fingernails.

No. It was better to sit here in the dark and be miserable. Dean would go on being handsome and mysterious and secretly really nice and he and Anna would get married and Cas would just weep continually for the rest of his life. That was probably the best-case scenario, when it all came down to it.

Cas's phone buzzed in his pocket, and he anxiously scrambled to take a look at it. It wasn't like he got a lot of texts, if somebody was to look through his phone history it would probably be something like Anna, Anna, Anna, Dad, Mom, Anna, Welcome to Verizon mobile.

"hey u ok?" The phone read. It was a number he didn't recognize. Well, maybe the universe had finally taken pity on him and wanted to see how he was doing. He jumped as the phone buzzed again in his hand. "srry this is Dean got yr # from Sammy"

Castiel's eyes widened. "No. No no no. Fuck. No." He muttered, then threw his phone across the room. It hit the wall with a loud cracking noise, which probably didn't bode well for his upgrade plan. Groaning in frustration, Cas smushed his face into a pillow as though this would somehow make it harder for him to think.

"Castiel?" He heard Anna call from down the hall. "Are you ok?"

"I'm fine! Everything's fine!" Cas shouted back, flinching at how guilty he sounded. "Don't worry, just uh, dropped something. I'm fine!"

This was very very bad.


	4. Chapter 4

Castiel had somehow managed to ride to school with his older sister without making eye contact with her or throwing up all over himself with guilt. Which was better than when he was four and had tried to hide the fact that he ate a whole stick of butter from her, although throwing up in that instance may have come from a variety of causes.

At lunchtime, Castiel decided to sit cross-legged on the floor of a seldom-used hallway outside of the gym, where he could eat his Tupperware of pasta salad with calamata olives and goat cheese in peace. It had been a while since the last time he sat out here, although during the first few weeks of school it had been is hiding place of choice. He remembered those nerve-wracking weeks of classes, when he'd looked out at the masses of cheerful high school students enjoying themselves and decided that he just couldn't handle it. Apart from a few teachers who pretended not to notice the weird kid sitting by himself as they passed by, he could usually get some privacy here.

But while the hallway was seldom used that didn't mean it was never used. Obnoxious laughter and a strong whiff of Axe body spray announced the arrival of a group of Castiel's classmates. Castiel tried to make himself as small and unnoticeable as possible against the hallway wall, but it was too late.

"Cassandra!" a pudgy blonde boy named Chad sneered, brilliantly and originally calling Castiel a woman's name in order to insult him, "You can't eat out here it's against the rules."

Castiel looked up at his classmates, a group of about six young men now wandering near to him. They were all moderately fit, tanned from sports, indistinguishable young men wearing some combination of khaki shorts and striped polo shirts. He wasn't doing anything to bother them. Surely this time they would just leave him alone. "I would appreciate it if you wouldn't tell a teacher." Castiel said, and continued, deadpan, a la Bartleby the Scrivener, "I'd prefer to sit out here today."

Chad was already snickering though and boisterously trying to get the guys around him to pay attention.

"What are you eating anyway? You're so fucking weird!" Chad laughed kind of desperately, eyes flashing to his friends for affirmation. The other boys, blessed with the quiet confidence that comes with being a moderately good looking jock in high school, went along with it. These guys had been raised with Chad, had been friends with him since they were about three years old, and the fact that he had grown into a real jerk wasn't quite enough to break those bonds. Chad was obviously not going to stop ragging on this kid, and they were on his side at this particular moment. "Maybe eating all that gay food is what turned you gay." Chad suggested, then shrieked with laughter at his own joke. His friends backed him with an obligatory chuckle.

Castiel's expression flattened out and he directed all of his attention to eating his lunch as quickly as possible.

"Hey, dude, you got a problem?" a gruff voice called out from down the hallway. Castiel tensed in recognition of Dean Winchester's voice, looking up, panicked, as his defender strode down the hallway towards them.

"Who are you?" Chad muttered. His expression was cautiously defiant. Dean towered over the pudgy bully, but Chad was still surrounded by his posse of dudes and they looked dangerously athletic.

"I'm Dean Winchester asshole, and you better just go to lunch ok?" Dean's voice had lowered to a threatening growl, and his shoulders were set like somebody who knew how to throw a punch's.

"Dude, Chad, let's just get out of here." Said a guy wearing a pink polo with a popped collar. He clearly outranked Cas's tormentor in the social ranking because everybody but Dean and Chad immediately relaxed and began moving away. Things were getting awkward. Nobody wanted to get suspended.

Chad gave another one of his aggressive little laughs, but he raised his hands in what looked like resignation and began to back up. Cas, who hadn't taken a breath pretty much since Dean showed up, realized that he had been holding his fork so tightly it had bent the plastic.

"Ok, whatever," Chad said, turning around. Dean was about to turn to Cas to make sure everything was ok, when Chad finished his thought.

"_Faggots._"

With a growl Dean sprang towards Chad to wipe that fucking smile off his face, but he never got the chance.

_Castiel _had launched himself from his seated position and with a rough grab and a shove had Chad pinned to the wall in less than 5 seconds.

"You are mean without being clever, you aren't funny, and you don't have any real friends." Castiel hissed at a stunned, panicky Chad who was clawing at Cas's arm trying to wiggle free. Cas was a rock though, and no matter how much Chad flailed he couldn't get out.

At this point Chad's "friends" had overcome their initial shock at the weird little guy actually defending himself, and had started running over to see what was going on. Dean managed to rip his eyes away from the stunningly transformed "in-charge" Castiel to address the group.

"Back the fuck up." Dean growled, shoving one of the bigger guys. In the next few seconds everything was punching and scuffling and grabbing and shouting. Castiel, figuring that he'd let Chad get out before he pissed himself, turned to find Dean fighting like a madman. He was hopelessly outnumbered by a whirlwind of douchebags, but he was putting up a good show. Cas ran over and wrapped his arms around Dean, restraining him, and trying to drag his sister's boyfriend out of the fray.

"HEY." Shouted a teacher, and everybody bolted. The crowd of jockish asshole boys disappeared down the hallway, sprinting through various escape routes. Well, everybody escaped save Dean who was still entangled in Cas's restraining grip.

"Mr. Singer," Castiel pleaded to his favorite English teacher, still holding back a furious Dean, "Please, they started all this, he was just trying to help."

Mr. Singer was glaring at the two boys, with the expression that usually comes immediately before a suspension when coming from a teacher, but his eyes flicked down to the pasta salad Cas had spilled onto the floor. He eyed Castiel and his friend. Dean had finally stopped trying to get away, but he was still fuming and looking down the hallway at where Chad and his gang had run.

"You eating in the hallway again, Castiel?" Singer asked.

"It's been a bad week, Mr. Singer." Castiel said, sheepishly.

"Who's this one?" Mr. Singer asked

"Dean Winchester." Cas said.

"I'm Cas's boyfriend." Dean elaborated.

Cas was struck by a sensation of lightheadedness, and he could not help but stare at Dean as though he had just announced that he was made entirely of ham and that the school was about to blow up. Mr. Singer raised an eyebrow.

"Are you? Well cool your jets son, because if I see any dumb stuff like what I just saw ever again your ass is OUT of this school, do you understand?"

"Yes sir." Dean muttered, rubbing his forehead.

Cas didn't respond, he was still floating somewhere in the stratosphere after Dean's announcement.

"Good." Mr. Singer's face still expressed nothing but annoyance, but he gave Castiel a stiff pat on the back in solidarity before he started to walk away down the hall. "Go eat your lunch in the darn cafeteria like a normal person." He called back to the sophomore as he stepped into his classroom.

Dean turned to Cas, his beautiful green eyes expressing nothing but empathy, and he touched Cas's arm in reassurance.

"You ok Cas?" He asked.

Castiel's eyes were wide with shock, his expression stunned. Moments ago he had been terrifying, but now he looked like he'd forgotten how to close his mouth. In other words, it was not immediately obvious to Dean whether or not Castiel was all right.

"I…" he said, looking down at where Dean was still touching his arm, "What?"

The last time Dean had seen Cas show this much emotion he had been sitting in his lap. Dean smirked just ever so slightly and touched the side of Cas's face, and Castiel's eyes, impossibly, grew even wider.

"Cas," Dean said, remembering the way Cas's whole demeanor had shifted once he was holding Chad to the wall, all fury and strength and… _fuck_, "Can we like, get out of here? And talk?"

"Dean?"

A beautiful red head stood at the end of Castiel's secret hallway, trembling slightly as she looked at her brother and her boyfriend standing so closely together. Cas jumped back like Dean's hand on his face had burned him, overwhelmed by guilt. Dean looked at his girlfriend, who was staring at her brother and her boyfriend, perched beautifully on the precipice between screaming and crying.

"Hey Anna." Dean said, his tone serious. "We should probably talk first. I guess."

The three Winchester men sat around their tiny kitchen table, with a half eaten grocery store pie as centerpiece. Dean was drawing little designs on his plate with the melted ice cream remains of his dessert, while his father and brother stared directly at him with expressions of utter incredulity. Sam broke the silence first.

"Hold up, you and Anna broke up because you…"

"I'm like bi or something. I don't know. I like her brother." Dean took a swig of his Root Beer like this was no thing. On his own earlier Dean had been trembling like a daisy thinking about telling his brother and father what had happened, but in front of both of them he could have been ordering pepperoni instead of mushrooms on a pizza.

Things had been considerably worse when he was telling them to Anna. He could still see the hurt expression on her face when had had told her about the Star Wars evening. The fact that she had so clearly been trying really hard not to cry had actually been worse than if she had just lost it.

"You're dating a boy?" John Winchester asked, just trying to pin the basics down.

"No, Cas flipped shit and said he couldn't date me because I used to date his sister and it's too weird." Dean looked miserably down at the table in front of him. Cas hadn't been able to make eye contact with him the whole time they had talked, he had made his ultimatum and left. The whole day had been total soap opera bullshit, and he was tired of feeling so many fucking emotions. He took another slug of root beer.

"So you wanted me to make friends with Cas so you could cheat on your girlfriend with him?" Sam asked.

"No! I wanted you to make friends with Cas because I don't want him to be bullied! Nice job with that by the way, Jesus." He rolled his eyes, irritated and defensive. "And don't call him Cas, I call him Cas, you don't get to call him Cas."

"So you're gay?" John Winchester asked for the second time. His expression was unreadable, so Dean couldn't quite tell if this was going to be a Burt Hummel moment or something considerably less sympathetic.

Dean looked down at his root beer again, pouring every ounce of effort he had into speaking coolly and calmly.

"I like dudes and girls." He said. Cas had probably felt like this coming out to his parents too. God, he should buy him more than just a cookie for being a jerk about that.

"But, you've always been such a…" John paused, trying to think of the word.

"Slut?" Sam suggested.

"Shh Sam. Um, Ladies man?" John asked with a hint of hope in his voice.

"Slut." Sam repeated.

"Damnit Sam, shh." John looked at his second youngest son with that irritated expression only Sam could milk out of him. Dean could hardly think of a time the two of them had been together without bickering. But he did not need that right now, he was going through some shit.

"Dad, I've always checked out dudes, I just never let myself think about it until Cas. I still like girls though, I just like dudes too. I think. I'm not sure, it's complicated." Dean sighed. "Not like it matters because I'm a huge asshole and Cas's never going to date me because it would be really shitty for Anna."

Dean eyed his father's beer.

"Could I have some of that?"

"No." John said. He had some dubious parenting methods, but apparently underage drinking was where he drew the line. He leaned back in his chair, staring at his son. Dean looked down sheepishly, unintentionally displaying his long eyelashes, and that small movement reminded John so strongly of Dean's mother that he had to look away for a second.

This was exactly the sort of shit these boys needed a mother for. John took a deep breath before he continued.

"Dean, I'm not going to lie to you, this whole situation is just out of my league. I don't know what I should say to you about this."

Dean stared at his plate, jaw clenched. He'd bought Cas a cookie? Fuck that. He'd make Cas a pie, that's what he'd do, he'd bake him a homemade friggin' pie.

"But Dean, I just want you to know that I love you, and your brother, no matter what." John Winchester said. "I don't have any idea what I can tell you about dating your girlfriend's brother, because that's just… that's ridiculous honestly. But I'm sure you'll figure it out."

With that he smiled compassionately at his son, and finished off his beer. Dean shrugged and finished his root beer. As far as Winchester family meetings went, this one was about average in the level of awkwardness. At least they weren't talking about their feelings anymore, thank fucking God.

Anna's laptop had a surprising amount of quality break-up songs, a fact she was taking advantage of, perched on her computer chair in her pjs scrolling through her iTunes and putting together a fairly epic playlist. She and Jo had stopped after school to pick up some ice cream and DVDs, and she had spent her evening at Jo's house, watching movies she liked while Jo's mother Ellen brought her more slices of pizza and rubbed her back comfortingly.

A very soft knock struck her door.

"Come in." Anna invited, toggling back and forth between Single Ladies and Kiss You Off.

"Anna." Castiel's distinctive voice greeted her from her door, the first time she had been addressed by him since before the weekend. She looked up from her laptop to see her little brother, standing in her doorway wearing a ratty t-shirt and pajama pants, holding a wrapped cookie in his hands, and staring at the ground like a shy toddler asked to say hello to a stranger.

"Hi Castiel" Anna said. Her face remained flat and emotionless, the way Castiel's usually was. Perhaps some things do run in families.

"Anna, I should never have kissed Dean." Castiel took a deep breath and looked up, meeting her beautiful clear eyes with his own. He extended the cookie in front of him. "I know this isn't enough."

Anna examined her little brother. His face was rife with poorly hidden misery. She hadn't seem him look like this since the night he knocked on her door and told her that he was pretty sure he was gay, and that he was almost positive that their parents were going to throw him out for it. She took the cookie with a frustrated sigh, then reached out and took her brother in her arms, enclosing him in a sort of bear hug that she hadn't given him since he was actually a little kid.

"Castiel, don't worry about it, ok?" She shook her head and looked into his utterly astonished face. A bemused laugh escaped her when she saw his panic. "Castiel, I had been planning on breaking up with Dean for a like a week."

Castiel pulled back a little bit further from Anna's hug. His eyes were wide, begging for her to continue.

" I don't know if you noticed but he was kind of being a dick boyfriend…" She paused, imagining her handsome boyfriend, er, ex, kissing her little brother. Nope, that was gonna be weird for a while. "For, I guess, reasons that you probably know more than me honestly. Ugh." She shook her head and recollected her thoughts, focusing on the panicky baby brother at hand, "ok Castiel, just don't beat yourself up about this ok?"

For a few seconds Castiel stood utterly still, absorbing the shock of this information.

"You were going to break up with _Dean_?" Castiel asked, clearly disbelieving.

Anna raised a skeptical eyebrow. "Wow, ok, yeah, I don't know what he did for you but he sure as hell wasn't doing that for me." Anna looked at her baby brother, remembering how worried she'd been about him for their first few weeks at this school. Ever since he'd started spending time with Dean he'd been more social, he'd stopped locking himself in his room and listening to depressing music, he'd like, got a life. "Castiel, if you want to date Dean…" She paused again. "Wait a few weeks?" She sighed.

Castiel actually gasped at this.

"I wasn't, no, Anna, I couldn't…" He sputtered.

"Let me tell you, he would totally be into it. Trust me." Anna continued, rolling her eyes. "He talked about how great you were for like 20 minutes when I was trying to dump his ass. Worst apology ever."

Castiel's face resumed its normal blank expression, which Anna knew signaled something close to contentment for her little brother. She hardly had time to be pleased with his happiness before she had the wind knocked out of her from a crushing hug.

"Thanks Anna." Cas whispered, voice muffled from his face being smushed into her collarbone.

"You'd do the same for me." Anna shut her eyes and sighed. "Now get the hell off me and let me brood for a while, 'kay?"

SUMMER:

Dean stared intently at the ragged basketball hoop in front of him at their local public courts, dribbling the ball several times in prep. He was pouring sweat, his dark t-shirt sticking to his back uncomfortably. He eyed the hoop again. Sam and him were playing PIG, and if Dean didn't get this last shot than Sam would win. He dribbled a couple more times.

"OH JUST GET IT OVER WITH ALREADY!" Sam shouted at him from off court, taking a swig from one of those fancy water bottles that look like they come from the future and athletes find so damn necessary.

Dean rolled his eyes in exasperation and took his shot. The ball arched up splendidly, before ricocheting off the side of the hoop and towards the ground, along with Dean's hopes of victory.

"WOOT WOOT!" Sam announced, throwing his arms in the air and running around his older brother in an overexcited victory circle. "P-I-G baby!"

"Whatever, you got lucky dude." Dean grumbled.

"I think the fact that he is on the basketball team and practices a lot more than you is why he was able to beat you so easily at this game." A gravelly voice from the sidelines suggested, honestly and without any judgment in its tone.

"Son of a bitch!" Dean gumbled. "What kind of a boyfriend are you?" Dean looked over at Castiel, who had been sitting at the edge of the court watching the game in its entirety, remaining completely silent until just now. Regardless of the heat, he was dressed in a white button up shirt and belted kakhi pants, and unlike Dean didn't appear to have broken a sweat.

"I'm not sure what kind of a boyfriend I am." Castiel responded, but he gave that little half smile that so rarely graced his expression, "But I think I'm a pretty good one, all things considered."

It was just too cute, and Dean couldn't help but jog over to the side of the court to wrestle Cas into a teasing headlock, Cas complaining all the while about how gross and sweaty Dean was. Dean kissed him right on the top of his adorable head, and Sam gave his usual sigh and continued practicing free throws like this wasn't happening.

"Hey!" A voice called out from a car at the side of the park. A pale face framed in gorgeous red hair peeked out of the window. "Lovebirds! It's too hot for this shit! Jo and I want ice cream. You in?" Anna kind of liked Dean better now that they weren't dating. She'd always thought of him as an incredibly attractive asshole that would look good standing next to her in prom pictures. But the way he looked at Cas, like he couldn't believe that somebody this great actually liked him, it was just to freaking cute to resent.

"Hell yeah!" Dean called out to his ex girlfriend. They were fairly comfortable together again, once Dean had stopped thinking about how weird their situation was. Anna had gotten over him with almost insulting rapidity, and it had only taken a month for the rest of Anna's family to stop making snide comments about him when he came over to pick Cas up or stay for dinner.

Sam, Dean, and Cas impossibly managed to squeeze themselves in the backseat of Anna's car and she headed off towards Dean and Sam's favorite ice cream place. Cas casually hooked his arm around Dean's, sweaty grossness be damned, and snuggled into his boyfriend slightly closer. Dean leaned down ever so slightly to whisper in Cas's ear.

"Later?" Dean asked.

"Definitely." Cas responded, and surreptitiously kissed Dean's cheek.

"Gross dudes." Sam said, too close to not have overheard the entire exchange.

"Shut the hell up Sammy." Dean teased, and surprised Castiel by tilting his face up and kissing him right on the lips in front of everyone. Cas recovered quickly though, closing his eyes and kissing back.

It was going to be a lovely summer.


End file.
